Synthesis of resorcinolic lipids bearing structural similarities to cytosporone A

Santos, Edson dos Anjos dos; Beatriz, Adilson; Lima, Dênis Pires de; Marques, Maria Rita; Leite, Carla Braga

doi:10.1590/s0100-40422009000700032

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…In addition to compounds 1 – 8 , two known phthalides [5,7-dimethoxyphthalide ( 9 ) 11 , 12 and 4,6-dimethoxyphthalide ( 10 ) 13 , 14 ], and one known naphthalenone [isosclerone ( 11 )] 15 were isolated and identified by comparison of NMR, HRMS, and optical rotation data (for 11 ) to the literature. This is the first report of 10 from a fungal source.…”

Section: Resultsmentioning

confidence: 99%

Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album

et al. 2014

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As part of an ongoing project to explore filamentous fungi for anticancer and antibiotic leads, eleven compounds were isolated and identified from an organic extract of the fungus Scytalidium album (MSX51631) using bioactivity-directed fractionation against human cancer cell lines. Of these, eight were a series of sorbicillinoid analogues (1–8), of which four were new [scalbucillin A (2), scalbucillin B (3), scalbucillin C (6), and scalbucillin D (8)], two were phthalides (9–10), and one was naphthalenone (11). Compounds (1–11) were tested in the MDA-MB-435 (melanoma) and SW-620 (colon) cancer cell lines. Compound 1 was the most potent with IC50 values of 1.5 and 0.5 μM, respectively, followed by compound 5, with IC50 values of 2.3 and 2.5 μM at 72 h. Compound 1 showed a 48-h IC50 value of 3.1 μM when tested against the lymphocytic leukemia cell line OSU-CLL, while the nearly identical compound 5 had almost no activity in this assay. Compounds 1 and 5 showed selective and equipotent activity against Aspergillus niger with minimum inhibitory concentration values of 0.05 and 0.04 μg/ml (0.20 and 0.16 μM), respectively. The in vitro hemolytic activity against sheep erythrocytes of compounds 1 and 5 was investigated and were found to provoke 10% hemolysis at 52.5 and 45.0 μg/ml, respectively, indicative of a promising safety factor.

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Section: Resultsmentioning

confidence: 99%

Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album

et al. 2014

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“…14 These possibilities led our research group to focus on the development of new herbicides based on natural products obtained from microbial sources, and we have recently reported the synthesis of cytosporone analogues with promising allelopathic activity. 15 In the present article, we report the total synthesis of cytosporones A (1), B (2), and C (3) through a short, high-yield synthetic route. All natural products and intermediates involved were tested for their potential inhibition of seed germination and plantule development of lettuce (Lactuca sativa L., cv.…”

Section: Staphylococcus Aureus Enterococcus Faecalis Andmentioning

confidence: 99%

Total synthesis and allelopathic activity of cytosporones A-C

Zamberlam¹,

Meza²,

Leite³

et al. 2012

J. Braz. Chem. Soc.

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A busca por herbicidas eficientes e ambientalmente corretos tem sido foco de numerosos estudos sobre a síntese de compostos isolados de fontes naturais. Citosporonas, as quais são lipídeos fenólicos isolados de fungos, apresentam notáveis propriedades biológicas. Este artigo relata a preparação das citosporonas A, B e C, através de uma rota sintética curta e com excelentes rendimentos. Os compostos sintetizados foram avaliados quanto às suas atividades alelopáticas em sementes de alface (Lactuca sativa L). Citosporona A e seu precursor metilado mostraram notável atividade alelopática, inibindo a germinação de sementes e crescimento das plântulas.The search for efficient, environmentally friendly herbicides has been the focus of numerous studies on the organic synthesis of compounds isolated from natural sources. Cytosporones, which are phenolic lipids isolated from fungi, exhibit noteworthy biological properties. This paper reports the preparation of cytosporones A-C from the same starting material through a short synthetic route, with good yields. All compounds were tested for allelopathic activity on lettuce (Lactuca sativa L) seeds. Cytosporone A and its methylated precursor showed remarkable allelopathic activity, inhibiting seed germination and plantule growth.

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A new synthetic resorcinolic lipid 3-Heptyl-3,4,6-trimethoxy-3H-isobenzofuran-1-one: Evaluation of toxicology and ability to potentiate the mutagenic and apoptotic effects of cyclophosphamide

Navarro

Beatriz

Meza

et al. 2014

European Journal of Medicinal Chemistry

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Synthesis of resorcinolic lipids bearing structural similarities to cytosporone A

Cited by 4 publications

References 5 publications

Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album

Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album

Total synthesis and allelopathic activity of cytosporones A-C

A new synthetic resorcinolic lipid 3-Heptyl-3,4,6-trimethoxy-3H-isobenzofuran-1-one: Evaluation of toxicology and ability to potentiate the mutagenic and apoptotic effects of cyclophosphamide

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